When we talk about the modern renaissance man, Mark Cuban may be the most fitting example. He’s dabbled in everything from running his own bar to creating a multi-billion dollar internet company. It can be hard to keep track of all the business ventures and investments he’s made over the decades. Through his position as a Shark on the hit show Shark Tank, he’s made hundreds of investments. We’ve sorted through the fluff to come to the 9 best Mark Cuban investments.

1- Amazon

Let’s start off with something current. Mark Cuban has a knack for understanding the stock markets and correctly foresaw the dot com bubble of the early 2000’s. In a change of tone however, Mark Cuban has recently come out saying that he thinks Amazon makes up a large portion of his portfolio and that it is the greatest company in the world. He loves that Amazon is making inroads into various markets and will soon end up competing with companies like Uber.

2- Netflix

In another bullish note for technology stocks, Cuban tweeted that along with Amazon, Netflix was one of the best companies to own today. He boldly predicted that the world would experience an unprecedented technological revolution in the next 10 years and that Netflix is primed to capitalize on that trend. He doesn’t always agree with Netflix CEO Reed Hastings but agrees that Hastings is the man for the job.

3- Cyber Dust

Clearly you can really see Cuban’s optimism for the future of technology. After the SEC launched an investigation into Cuban for potential insider trading (See Mamma.com below), Cuban became a staunch advocate for privacy. He brought that his ideas to fruition with the development of Cyber Dust, his new messaging app launched in 2014 that aimed to protect that privacy of users. Although an applaudable effort by Cuban to breaking into the lucrative privacy protection industry, the app was largely considered a failure. Though the app received initial buzz, numerous user interface problems and an overall shaky idea caused but ultimately flicker and die out.

4- 2929 Entertainment

Cuban brought his signature zeal to the film industry with his founding of 2929 Entertainment in 2003. Along with his college friend Tom Wagner, Cuban set out to make films that were outside of the traditional Hollywood bubble. Together, they began to finance the production of independent movies and were able to pump out some pretty good ones for that matter. Their ‘Good night, and Good Luck’ brought in over $30 million at the box office and was nominated for best picture at the Academy Awards.

5- Mamma.com

Mark Cuban is pretty good at investing. Maybe a little too good… At least, that’s what the SEC thought. After Cuban ditched internet company Mamma.com right before an offer was given to the company that would dilute his shares, the SEC brought forward charges of insider trading in 2004. The case dragged on for nearly a decade and it was only brought to a conclusion in 2013. Due to the fact that the SEC had minimal evidence, a Texas jury found Cuban innocent on charges of insider trading.

6- Dallas Mavericks

Never one to shy away from something he didn’t totally understand, Cuban, flush with cash after selling broadcast.com, decided to buy the NBA team Dallas Mavericks in 2000 for the sum of $285 million. He brought not only his dogged enthusiasm, but his organizational skill-set too. At the time the Mavericks were considered one of the worst teams in the league. Cuban reorganized the team and instilled a new sense of pride within them, helping propel them to the NBA finals in 2006. It wasn’t only great for Mavericks fan; Cuban turned the Mavericks into one of his greatest investments. Buying it for only $285 million, the Mavericks are now worth an estimated $1.15 billion.

7- Broadcast.com

Cuban made the largest chunk of his wealth from this company. Annoyed that he couldn’t listen to his alma matters college basketball games, he decided to find a solution. With long time buddy Tom Wagner, he began to stream Indiana Hoosier games. It spread like wildfire and began to stream hundreds of different games. Caught up in the internet frenzy that was characteristic of the 90’s, Yahoo decided to buy the company at 57 times revenue for a whopping $5.7 billion dollars. After the dotcom bubble the value of broadcast.com plummeted but it didn’t matter for Cuban. He had gotten off like a bandit making over a billion dollars on the deal.

8-Microsolutions

This was the first company Cuban started that got acquired. He decided to start the business after being fired from a company for disobeying the orders of the CEO. Cuban knew then that he didn’t want a boss- he wanted to be the boss. He saw the need that corporations had to make the transition to the digital world and started Microsolutions as well, a solution. (As he’d later find out, the solution was so micro). He acted as a PC consultant and helped companies navigate the uncertain digital age. After Microsolutions reached $30 million in sales, Cuban sold the company to Compuserve for a nice $6 million.

9- Motley’s Pub

Although not one of Cuban’s most famous investments, it does show the entrepreneurial spirit that was so evident in him. In order to make ends meet and pay for his college tuition, Cuban scrapped together $15,000 and started up his own bar. It immediately became popular with university students and gave Cuban the chance to invest in himself. He learned how to be a leader and learned the ropes of business firsthand- a skill that would be invaluable for his future career.

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